JP3699464B2 - Diimonium salt compound, near-infrared absorption filter using the same, and optical information recording medium - Google Patents
Diimonium salt compound, near-infrared absorption filter using the same, and optical information recording medium Download PDFInfo
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- JP3699464B2 JP3699464B2 JP2003510997A JP2003510997A JP3699464B2 JP 3699464 B2 JP3699464 B2 JP 3699464B2 JP 2003510997 A JP2003510997 A JP 2003510997A JP 2003510997 A JP2003510997 A JP 2003510997A JP 3699464 B2 JP3699464 B2 JP 3699464B2
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- compound
- infrared absorption
- ion
- absorption filter
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- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- CPBQJMYROZQQJC-UHFFFAOYSA-N helium neon Chemical compound [He].[Ne] CPBQJMYROZQQJC-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229910052809 inorganic oxide Inorganic materials 0.000 description 1
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- 238000009413 insulation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000007733 ion plating Methods 0.000 description 1
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 230000007257 malfunction Effects 0.000 description 1
- DZVCFNFOPIZQKX-LTHRDKTGSA-M merocyanine Chemical compound [Na+].O=C1N(CCCC)C(=O)N(CCCC)C(=O)C1=C\C=C\C=C/1N(CCCS([O-])(=O)=O)C2=CC=CC=C2O\1 DZVCFNFOPIZQKX-LTHRDKTGSA-M 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- MEFBJEMVZONFCJ-UHFFFAOYSA-N molybdate Chemical compound [O-][Mo]([O-])(=O)=O MEFBJEMVZONFCJ-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-M periodate Chemical compound [O-]I(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-M 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 229920001568 phenolic resin Polymers 0.000 description 1
- 150000004986 phenylenediamines Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229940085991 phosphate ion Drugs 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
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- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920001225 polyester resin Polymers 0.000 description 1
- 239000004645 polyester resin Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000009719 polyimide resin Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 1
- 239000004810 polytetrafluoroethylene Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920002620 polyvinyl fluoride Polymers 0.000 description 1
- 239000005033 polyvinylidene chloride Substances 0.000 description 1
- 229920002981 polyvinylidene fluoride Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- RGBXDEHYFWDBKD-UHFFFAOYSA-N propan-2-yl propan-2-yloxy carbonate Chemical compound CC(C)OOC(=O)OC(C)C RGBXDEHYFWDBKD-UHFFFAOYSA-N 0.000 description 1
- WVIICGIFSIBFOG-UHFFFAOYSA-N pyrylium Chemical compound C1=CC=[O+]C=C1 WVIICGIFSIBFOG-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 150000003658 tungsten compounds Chemical class 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/208—Filters for use with infrared or ultraviolet radiation, e.g. for separating visible light from infrared and/or ultraviolet radiation
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/02—Optical fibres with cladding with or without a coating
- G02B6/02057—Optical fibres with cladding with or without a coating comprising gratings
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
- G02B6/02—Optical fibres with cladding with or without a coating
- G02B6/02057—Optical fibres with cladding with or without a coating comprising gratings
- G02B6/02076—Refractive index modulation gratings, e.g. Bragg gratings
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Optical Filters (AREA)
- Optical Record Carriers And Manufacture Thereof (AREA)
Description
【０００１】
【技術分野】
本発明は、耐熱性に優れた、近赤外線吸収能を有するジイモニウム塩化合物、近赤外線吸収フィルター及び近赤外線吸収組成物、並びに、光情報記録媒体に関し、特に、該近赤外線吸収フィルターからなる、プラズマディスプレーパネル用の近赤外線吸収フィルターに関する。
【０００２】
【背景技術】
従来、近赤外線吸収剤であるジイモニウム塩化合物は、近赤外線吸収フィルター、断熱フィルム及びサングラス等に広く利用されている。しかしながら、従来のジイモニウム塩化合物においては、末端基が直鎖のアルキル基を有する化合物が多く、これらの化合物を用いる近赤外線吸収フィルターは、一般に、熱及び光に対して物質が変化しやすい等の原因から、近赤外線吸収能が低下するという問題があった。特に熱に対しては、分解に伴いフィルター自身の可視透過率が低下し、その色目も緑みを帯びてくるという重大な問題があった。近赤外線吸収フィルターは、プラズマディスプレーパネルにも用いられる。プラズマディスプレーパネルは、プラズマ発光を利用して画像を表示するパネルであるが、そのプラズマの発光には赤外線領域（８００〜１１００ｎｍ）の光も含まれるため、パネルの周辺に存在し得る様々な赤外線を利用した機器、例えばリモコン、自動ドア、進入感知機等の誤作動をなくすために、近赤外線吸収フィルターを用いて赤外領域の光をカットする必要がある。しかし、従来の近赤外線吸収剤では、上記のような理由から、満足できるフィルターを提供できないという問題があった。
【０００３】
また、有機色素を含有する光記録媒体、特に、１回のみ記録可能なＣＤ−ＲやＤＶＤ−Ｒ等の光ディスク及び光カード等に利用する色素として、シアニン系色素等の有機色素が種々提案されているが、一般に、それらの色素が光に対して変化しやすい等の原因から、記録再生特性及び保存安定性が低下するという問題があった。この様な問題の解決を目的とする手段として、すでに、特公平６−２６０２８や特開平１−９９８８５等に記載の如く、直鎖上の末端基を有するジイモニウム塩等を添加することが知られている。しかしながら、これらの化合物を用いて作製した記録媒体について耐熱試験及び耐湿熱試験を行った場合、一般にジイモニウム塩等が先に劣化してしまい、その後の耐光試験においてシアニン系色素の劣化が極端に悪くなるという問題があった。
【０００４】
【発明が解決しようとする課題】
本発明はこの様な状況に鑑みてなされたものであり、本発明の目的は、従来の直鎖状アルキル基を有するジイモニウム塩に比較して、安定性、特に耐熱性が向上した近赤外線吸収化合物（ジイモニウム塩）、そのような近赤外線吸収化合物を用いて作製した、プラズマディスプレーパネル用の近赤外線吸収フィルターに好適な耐熱性が向上した近赤外線吸収フィルター、及び光記録媒体を提供することにある。
【０００５】
【発明の開示】
本発明者らは前記したような課題を解決すべく鋭意努力した結果、下記式（１）の構造を有する近赤外線吸収化合物が優れた安定性、特に優れた耐熱性を有することを見出し、本発明を完成した。すなわち本発明は、
（１） 下記式（１）：
【０００６】
【化２】
で示される少なくとも一種の化合物を含有することを特徴とする近赤外線吸収フィルター；
（２） 環Ａ及びＢの１,４−位以外が無置換であるか、又は置換基として１〜４個のハロゲン原子、低級アルキル基、低級アルコキシ基、シアノ基及び／又はヒドロキシル基を有する、上記（１）に記載の近赤外線吸収フィルター；
（３） Ｒ１〜Ｒ８における分岐鎖状アルキル基が、１−メチルエチル基、１,１−ジメチルエチル基、１−メチルプロピル基、２−メチルプロピル基、１−メチルブチル基、２−メチルブチル基、３−メチルブチル基、又は２−エチルブチル基である、上記（１）又は（２）に記載の近赤外線吸収フィルター；
（４） プラズマディスプレーパネル用である、上記（１）から（３）のいずれかに記載の近赤外線吸収フィルター；
（５） 樹脂中に式（１）で表される化合物を添加してなることを特徴とする近赤外線吸収組成物；
（６） 下記式（１）：
【０００７】
【化３】
【０００８】
【化４】
で表されるジイモニウム塩化合物；及び
（７） 上記（６）に記載の少なくとも一種のジイモニウム塩化合物を記録層に含有することを特徴とする光情報記録媒体；
に関する。
【０００９】
【発明の実施の形態】
本発明の近赤外線吸収フィルターは、一般式（１）で示される構造の少なくとも一種の化合物を使用してなるものである。一般式（１）において、環Ａ及びＢには、１,４−位以外に１〜４個の置換基を有していても、いなくても良い。結合しうる置換基としては、例えば、ハロゲン原子、ヒドロキシル基、低級アルコキシ基、シアノ基、及び低級アルキル基等が挙げられる。ハロゲン原子としては、例えば、フッ素原子、塩素原子、臭素原子、及びヨウ素原子等が挙げられる。低級アルコキシ基としては、例えば、メトキシ基、エトキシ基等のＣ１〜Ｃ５のアルコキシ基が挙げられ、低級アルキル基としては、例えば、メチル基、エチル基等のＣ１〜Ｃ５のアルキル基が挙げられる。好ましくは、Ａ及びＢが何れも置換基を有していないか、又は、ハロゲン原子（特に塩素原子、臭素原子）、メチル基若しくはシアノ基で置換されているものが好ましい。尚、Ｂに置換基を有する場合は、４つのＢ環が全て同じであるもの、更に、置換基の位置は、フェニレンジアミン骨格に結合する窒素原子に対してｍ−位であるものが合成上好ましい。更に、環Ａ及びＢには、１,４−位以外に置換基を有していないものが合成上好ましい。
【００１０】
一般式（１）において、Ｒ１〜Ｒ８はそれぞれ同じであっても異なっていても良く、その少なくとも１つは分岐鎖状アルキル基であり、残りは、置換基を有してもよい炭素数１〜８の直鎖状アルキル基を表す。
【００１１】
このような分岐鎖状アルキル基の具体例としては、１−メチルエチル基（ｉ−プロピル基）、１,１−ジメチルエチル基（ｔ−ブチル基）、１−メチルプロピル基（ｓｅｃ−ブチル）、１,１−ジメチルプロピル基、２−メチルプロピル基（ｉｓｏ−ブチル基）、１,２−ジメチルプロピル基、２,２−ジメチルプロピル基、１−メチルブチル基、２−メチルブチル基、３−メチルブチル基（ｉｓｏ−アミル基）、１,１−ジメチルブチル基、２,２−ジメチルブチル基、３,３−ジメチルブチル基、１,２−ジメチルブチル基、及び２−エチルブチル基等の、炭素数１〜２０のアルキル基、好ましくは炭素数１〜１０のアルキル基が挙げられる。
【００１２】
Ｒ１〜Ｒ８における、分岐鎖状アルキル基以外の残りの置換基は、好ましくは、置換基を有してもよい炭素数１〜８の直鎖状アルキル基から選択される。これらの直鎖状アルキル基としては、具体的には、エチル基、ｎ−プロピル基及びｎ−ブチル基等が挙げられ、これらの基に結合し得る置換基としては、シアノ基；ヒドロキシル基；フッ素原子、塩素原子、臭素原子等のハロゲン原子；メトキシ基、エトキシ基、ｎ−プロポキシ基、ｎ−ブトキシ基等の炭素数１〜６のアルコキシ基；メトキシメトキシ基、エトキシメトキシ基、メトキシエトキシ基、エトキシエトキシ基、メトキシプロポキシ基、メトキシブトキシ基、エトキシブトキシ基等の炭素数２〜８のアルコキシアルコキシ基；メトキシメトキシメトキシ基、メトキシメトキシエトキシ基、メトキシエトキシエトキシ基、エトキシエトキシエトキシ基等の炭素数３〜１５のアルコキシアルコキシアルコキシ基；アリルオキシ基；フェノキシ基、トリルオキシ基、キシリルオキシ基、ナフチルオキシ基等の炭素数６〜１２のアリールオキシ基；メトキシカルボニル基、エトキシカルボニル基、ｎ−プロポキシカルボニル基、イソプロポキシカルボニル基、ｎ−ブトキシカルボニル基等の炭素数２〜７のアルコキシカルボニル基；メチルカルボニルオキシ基、エチルカルボニルオキシ基、ｎ−プロピルカルボニルオキシ基、ｎ−ブチルカルボニルオキシ基等の炭素数２〜７のアルキルカルボニルオキシ基；及び、メトキシカルボニルオキシ基、エトキシカルボニルオキシ基、ｎ−プロポキシカルボニルオキシ基、ｎ−ブトキシカルボニルオキシ基等の炭素数２〜７のアルコキシカルボニルオキシ基等が挙げられる。
【００１３】
上記したＲ１〜Ｒ８の分岐状アルキル置換基のうち、好ましいものとしては、例えば、１−メチルエチル基、１,１−ジメチルエチル基、１−メチルプロピル基、２−メチルプロピル基、１−メチルブチル基、２−メチルブチル基、３−メチルブチル基、及び２−エチルブチル基等が挙げられる。
【００１４】
Ｘは電荷を中和するのに必要なアニオンであり、アニオンが２価である場合には１分子、アニオンが１価の場合には２分子が必要になる。これらのアニオンは、例えば、有機酸アニオン又は無機アニオン等から選択される。具体的には、有機酸アニオンとしては、例えば、酢酸イオン、乳酸イオン、トリフルオロ酢酸イオン、プロピオン酸イオン、安息香酸イオン、シュウ酸イオン、コハク酸イオン、ステアリン酸イオン等の有機カルボン酸イオン；メタンスルホン酸イオン、トルエンスルホン酸イオン、ナフタレンモノスルホン酸イオン、ナフタレンジスルホン酸イオン、クロロベンゼンスルホン酸イオン、ニトロベンゼンスルホン酸イオン、ドデシルベンゼンスルホン酸イオン、ベンゼンスルホン酸イオン、エタンスルホン酸イオン、トリフルオロメタンスルホン酸イオン等の有機スルホン酸イオン；及び、テトラフェニルホウ酸イオン、ブチルトリフェニルホウ酸イオン等の有機ホウ酸イオン等が挙げられ、好ましくは、トリフルオロメタンスルホン酸イオン、トルエンスルホン酸イオン等のアルキルスルホン酸イオン及びアルキルアリールスルホン酸イオンが挙げられる。
【００１５】
無機アニオンとしては、例えば、フッ素イオン、塩素イオン、臭素イオン、ヨウ素イオン等のハロゲンイオン；チオシアン酸イオン、ヘキサフルオロアンチモン酸イオン、過塩素酸イオン、過ヨウ素酸イオン、硝酸イオン、テトラフルオロホウ酸イオン、ヘキサフルオロリン酸イオン、モリブデン酸イオン、タングステン酸イオン、チタン酸イオン、バナジン酸イオン、リン酸イオン、及びホウ酸イオン等が挙げられ、好ましいものとしては、過塩素酸イオン、ヨウ素イオン、テトラフルオロホウ酸イオン、ヘキサフルオロリン酸イオン、及びヘキサフルオロアンチモン酸イオン等が挙げられる。
【００１６】
これらのアニオンのうち好ましいものとしては、例えば、過塩素酸イオン、ヨウ素イオン、テトラフルオロホウ酸イオン、ヘキサフルオロリン酸イオン、ヘキサフルオロアンチモン酸イオン、トリフルオロメタンスルホン酸イオン、及びトルエンスルホン酸イオン等が挙げられる。
【００１７】
式（２）において、ｎは１〜１７の整数であり、好ましくは１〜７である。Ｒは分岐鎖状アルキル基であり、式（２）全体としての炭素数は４〜２０である。
【００１８】
次に、本発明の一般式（１）で示される近赤外線吸収化合物の具体例を表１〜３に示す。表１〜３中、ｉ−はｉｓｏ−、ｓ−はｓｅｃ−、ｔ−はｔｅｒｔ−のように分岐の状態を表し、ＴｓＯはトルエンスルホン酸イオンを表す。また、Ａ及びＢに関し、１,４−位以外が無置換の場合は「４Ｈ」と表記する。また、Ｒ１〜Ｒ８に関し、Ｒ１〜Ｒ８が全てｉｓｏ−ブチル基である場合、即ち、（Ｒ１,Ｒ２）、（Ｒ３,Ｒ４）、（Ｒ５,Ｒ６）及び（Ｒ７,Ｒ８）の４組の置換基の組み合わせが全てｉｓｏ−ブチル基である場合には「４（ｉ−Ｃ４Ｈ９，ｉ−Ｃ４Ｈ９）」と略記し、同様に、全てｉｓｏ−アミル基（−Ｃ２Ｈ４ＣＨ（ＣＨ３）２）である場合には「４（ｉ−Ｃ５Ｈ11，ｉ−Ｃ５Ｈ11）」と略記する。また、Ｒ１〜Ｒ８のうち、例えば、１つがｎ−ブチル基で残りがｉｓｏ−ブチル基である場合、即ち、４組の置換基の組み合わせの一つにｎ−ブチルが含まれ、残りの３組が全てｉｓｏ−ブチル基である場合には「３（ｉ−Ｃ４Ｈ９，ｉ−Ｃ４Ｈ９）（ｉ−Ｃ４Ｈ９，ｎ−Ｃ４Ｈ９）」と略記する。
【００１９】
尚、化合物Ｎｏ.２３及び２４は、４つのＢ環が全て同じであり、置換基の位置はフェニレンジアミン骨格に結合する窒素原子に対してｍ−位である。
【００２０】
【表１】
【表２】
【表３】
本発明の近赤外線吸収フィルターに使用される一般式（１）で表される化合物は、例えば特公昭４３−２５３３５号公報に記載された次の様な方法で得ることができる。即ち、ｐ−フェニレンジアミンと１−クロロ−４−ニトロベンゼンをウルマン反応させて得られた生成物を還元することにより得られる下記式（３）：
【００２４】
【化５】
で表されるアミノ体を、有機溶媒中、好ましくはＤＭＦ、ＤＭＩ又はＮＭＰ等の水溶性極性溶媒中、３０〜１６０℃、好ましくは５０〜１４０℃で、所望のＲ１〜Ｒ８に対応するハロゲン化化合物（例えば、Ｒ１がｉ−Ｃ４Ｈ９のときはＢｒＣＨ２ＣＨ（ＣＨ３）２）と反応させて、全ての置換基（Ｒ１〜Ｒ８）が同一である化合物（以下、全置換体と記す）を得ることができる。また、全置換体以外の化合物を合成する場合、例えばＮｏ.２５の化合物を合成する場合には、先に所定のモル数（上記式（３）のアミン体１モル当たり７モル）の試薬（ＢｒＣＨ２ＣＨ（ＣＨ３）２）と反応させてＲ１〜Ｒ８のうち７つにｉｓｏ−ブチル基を導入した後、残りの置換基（ｎ−ブチル基）を導入するのに必要なモル数（上記式（３）のアミン体１モル当たり１モル）の対応する試薬（ＢｒＣ４Ｈ９）と反応させる。例示したＮｏ.２５の化合物の製造方法と同様の方法により、全置換体以外の任意の化合物を得ることができる。
【００２５】
その後、上記で合成した化合物を、有機溶媒中、好ましくはＤＭＦ、ＤＭＩ又はＮＭＰ等の水溶性極性溶媒中、０〜１００℃、好ましくは５〜７０℃で、式（１）のＸに対応する酸化剤（例えば銀塩）を添加して酸化反応を行う。酸化剤の当量を２当量にすれば本発明の一般式（１）で表されるジイモニウム塩化合物が得られ、１当量にすれば、一価のアミニウム塩化合物（以下アミニウム体と記す）が得られる。
【００２６】
また、上記で合成した化合物を硝酸銀、過塩素酸銀、塩化第二銅等の酸化剤で酸化した後、その反応液に、所望のアニオンの酸もしくは塩を添加して塩交換を行う方法によっても、一般式（１）で表される化合物を合成することが出来る。
【００２７】
本発明の近赤外線吸収フィルターは、上記の近赤外線吸収化合物を含有する層を基材上に設けたものでも良く、また基材自体が近赤外線吸収化合物を含有する樹脂組成物（又その硬化物）からなる層であっても良い。基材としては、一般に近赤外線吸収フィルターに使用し得るものであれば特に制限されないが、通常、樹脂製の基材が使用される。近赤外線吸収化合物含有層の厚みは一般に０.１μｍ〜１０ｍｍ程度であるが、近赤外線カット率等の目的に応じて適宜決定される。また、近赤外線吸収化合物の含有量も、目的とする近赤外線カット率に応じて適宜決定される。
【００２８】
基材となる樹脂としては、樹脂板又は樹脂フィルムに成形した場合、できるだけ透明性の高いものが好ましく、具体例として、ポリエチレン、ポリスチレン、ポリアクリル酸、ポリアクリル酸エステル、ポリ酢酸ビニル、ポリアクリロニトリル、ポリ塩化ビニル、ポリフッ化ビニル等のビニル化合物、及びそれらのビニル化合物の付加重合体；ポリメタクリル酸、ポリメタクリル酸エステル、ポリ塩化ビニリデン、ポリフッ化ビニリデン、ポリシアン化ビニリデン、フッ化ビニリデン／トリフルオロエチレン共重合体、フッ化ビニリデン／テトラフルオロエチレン共重合体、シアン化ビニリデン／酢酸ビニル共重合体、等のビニル化合物又はフッ素系化合物の共重合体；ポリトリフルオロエチレン、ポリテトラフルオロエチレン、ポリヘキサフルオロプロピレン等のフッ素を含む樹脂；ナイロン６、ナイロン６６等のポリアミド；ポリイミド；ポリウレタン；ポリペプチド；ポリエチレンテレフタレート等のポリエステル；ポリカーボネート；ポリオキシメチレン等のポリエーテル；エポキシ樹脂；ポリビニルアルコール；及びポリビニルブチラール等が挙げられる。
【００２９】
本発明の近赤外線吸収フィルターを作製する方法としては、特に限定されるものではないが、例えば次の方法が利用できる。例えば、（１）樹脂に上記の近赤外線吸収化合物を混練し、加熱成形して樹脂板又はフィルムを作製する方法；（２）上記化合物と樹脂モノマー又は樹脂モノマーの予備重合体を重合触媒の存在下にキャスト重合し、樹脂板又はフィルムを作製する方法；（３）上記化合物を含有する塗料を作製し、透明樹脂板、透明フィルム、又は透明ガラス板にコーティングする方法；及び、（４）上記化合物を接着剤に含有させて、合わせ樹脂板、合わせ樹脂フィルム、又は合わせガラス板を作製する方法等である。
【００３０】
（１）の作製方法としては、用いる樹脂によって加工温度、フィルム化（樹脂板化）条件等が多少異なるが、通常、本発明の化合物を基材樹脂の粉体又はペレットに添加し、１５０〜３５０℃に加熱、溶解させた後、成形して樹脂板を作製するか、又は、押し出し機によりフィルム化（樹脂板化）する方法等が挙げられる。上記の近赤外線吸収化合物の添加量は、作製する樹脂板又はフィルムの厚み、吸収強度、可視光透過率等によって異なるが、一般的に、バインダー樹脂の重量に対して、０.０１〜３０重量％、好ましくは０.０３〜１５重量％の量で使用される。
【００３１】
上記の化合物と樹脂モノマー又は樹脂モノマーの予備重合体を重合触媒の存在下にキャスト重合して作製する（２）の方法においては、それらの混合物を型内に注入し、反応させて硬化させるか、又は、金型に流し込んで型内で硬い製品となるまで固化させて成形する。多くの樹脂がこの方法で成形可能であり、その様な樹脂の具体例として、アクリル樹脂、ジエチレングリコールビス（アリルカーボネート）樹脂、エポキシ樹脂、フェノール−ホルムアルデヒド樹脂、ポリスチレン樹脂、及びシリコン樹脂等が挙げられる。その中でも、硬度、耐熱性、耐薬品性に優れたアクリルシートが得られるメタクリル酸メチルの塊状重合によるキャスティング法が好ましい。
【００３２】
重合触媒としては公知のラジカル熱重合開始剤が利用でき、例えば、ベンゾイルパーオキシド、ｐ−クロロベンゾイルパーオキシド、ジイソプロピルパーオキシカーボネート等の過酸化物、及びアゾビスイソブチロニトリル等のアゾ化合物が挙げられる。その使用量は、混合物の総量に対して、一般的に０.０１〜５重量％である。熱重合における加熱温度は、一般的に４０〜２００℃であり、重合時間は、一般的に３０分〜８時間程度である。また熱重合以外に、光重合開始剤や増感剤を添加して光重合する方法も利用できる。
【００３３】
（３）の方法としては、本発明で使用する化合物をバインダー樹脂及び有機溶媒に溶解させて塗料化する方法、及び、本発明の化合物を微粒子化して水に分散し、水系塗料とする方法等がある。前者の方法では、例えば、脂肪族エステル樹脂、アクリル系樹脂、メラミン樹脂、ウレタン樹脂、芳香族エステル樹脂、ポリカーボネート樹脂、ポリビニル系樹脂、脂肪族ポリオレフィン樹脂、芳香族ポリオレフィン樹脂、ポリビニルアルコール樹脂、ポリビニル変性樹脂等、又はそれらの共重合樹脂をバインダーとして用いることができる。
【００３４】
溶媒としては、ハロゲン系、アルコール系、ケトン系、エステル系、脂肪族炭化水素系、芳香族炭化水素系、エーテル系の溶媒、又はそれらの混合物の溶媒を用いることができる。本発明の近赤外線吸収化合物の濃度は、作製するコーティングの厚み、吸収強度、可視光透過率によって異なるが、バインダー樹脂に対して、一般的に０.１〜３０重量％である。
【００３５】
このように作製した塗料を用いて、透明樹脂フィルム、透明樹脂板、又は透明ガラス等の上、にスピンコーター、バーコーター、ロールコーター、又はスプレー等でコーティングして、近赤外線吸収フィルターを得ることができる。
【００３６】
（４）の方法において、接着剤としては、一般的なシリコン系、ウレタン系、アクリル系等の樹脂用又は合わせガラス用のポリビニルブチラール接着剤、エチレン−酢酸ビニル系接着剤等の合わせガラス用の公知の透明接着剤が使用できる。本発明の化合物を０.１〜３０重量％添加した接着剤を用いて透明な樹脂板同士、樹脂板と樹脂フィルム、樹脂板とガラス、樹脂フィルム同士、樹脂フィルムとガラス、又は、ガラス同士を接着して、フィルターを作製する。
【００３７】
尚、それぞれの方法で混練、混合の際、紫外線吸収剤、可塑剤等の、樹脂成形に用いる通常の添加剤を加えても良い。
【００３８】
このように、（１）から（４）のそれぞれの方法において、樹脂中に式（１）で表される本発明化合物を添加した近赤外線吸収組成物も、本発明に含まれる。
【００３９】
本発明の近赤外線吸収フィルターは、好ましくは、一般式（１）で表されるジイモニウム塩化合物を用いるが、対応する構造のアミニウム体を用いてもよい。アミニウム体を用いる場合、アミニウム体単独でもよいし、一般式（１）のジイモニウム化合物と併用してもよい。更に、他の近赤外線吸収化合物と混ぜて作製しても良い。併用し得る他の近赤外線吸収化合物としては、例えば、フタロシアニン系、シアニン系色素、及びジチオールニッケル錯体等が挙げられる。また、無機金属の近赤外線吸収化合物も併用し得、そのような無機金属としては、例えば、金属銅、硫化銅又は酸化銅等の銅化合物、酸化亜鉛を主成分とする金属混合物、タングステン化合物、ＩＴＯ、及びＡＴＯ等が挙げられる。
【００４０】
また、フィルターの色調を変えるために、可視領域に吸収を持つ色素を、本発明の効果を阻害しない範囲で加えることも好ましい。また、調色用色素のみを含有するフィルターを作製し、後で本発明の近赤外線吸収フィルターを張り合わせることもできる。
【００４１】
この様な近赤外線吸収フィルターは、ディスプレーの前面板に用いられる場合には、可視光の透過率は高いほど良く、少なくとも４０％以上、好ましくは５０％以上の透過率が必要である。近赤外線のカット領域は、好ましくは８００〜９００ｎｍ、より好ましくは８００〜１０００ｎｍであり、その領域の近赤外線の平均透過率が５０％以下、より好ましくは３０％以下、更に好ましくは２０％以下、特に好ましくは１０％以下になることが望ましい。したがって、一般に可視光の透過率が低い傾向にあるアミニウム体は用いず、一般式（１）のジイモニウム化合物を用いることが好ましい。
【００４２】
本発明の光記録媒体は、基板上に記録層を有するものであり、該記録層は一般式（１）のジイモニウム化合物及び／又はアミニウム体を少なくとも1種含有することを特徴とする。一般式（１）のジイモニウム化合物及び／又はアミニウム体をそれぞれ単独で使用してもよいが、必要に応じて一般式（１）の化合物及び／又はアミニウム体から選ばれる化合物をそれぞれ１種以上混合して使用してもよい。
【００４３】
本発明の光記録媒体の記録層には、一般式（１）のジイモニウム化合物及び／又はアミニウム体が単独で含有されていてもよく、またバインダー等の各種添加剤と混合して含有されていてもよい。この場合、一般式（１）のジイモニウム化合物及び／又はアミニウム体により情報が記録される。
【００４４】
更に、一般式（１）のジイモニウム化合物及び／又はアミニウム体を、有機色素により情報が記録される光記録媒体の記録層に含有させることによって、該光記録媒体の耐光性を向上させることができる。このような光記録媒体も本発明の光記録媒体の一種である。
【００４５】
一般式（１）のジイモニウム化合物及び／又はアミニウム体を耐光性向上の為に使用する光記録媒体において、これらの化合物と併用しうる有機色素としては、一般的に知られている色素、例えば、シアニン系色素、スクワリリウム系色素、インドアニリン系色素、フタロシアニン系色素、アゾ系色素、メロシアニン系色素、ポリメチン系色素、ナフトキノン系色素、及びピリリウム系色素等が挙げられる。
【００４６】
これらの有機色素１モルに対して、一般式（１）のジイモニウム化合物及び／又はアミニウム体は、一般的に０.０１〜１０モル、好ましくは０.０３〜３モル使用される。
【００４７】
本発明の光記録媒体は、基板上に一般式（１）のジイモニウム化合物及び／又はアミニウム体と所望により色素を含有する記録層を設けたもので、必要に応じ、反射層、保護層が設けられる。基板としては既知のものを任意に使用することが出来る。例えば、ガラス板、金属板又はプラスチック板もしくはフィルム等が挙げられ、これらを製造するためのプラスチックとしては、アクリル樹脂、ポリカーボネート樹脂、メタクリル樹脂、ポリスルホン樹脂、ポリイミド樹脂、非晶質ポリオレフィン樹脂、ポリエステル樹脂、ポリプロピレン樹脂等が挙げられる。基板の形状については、ディスク状、カード状、シート状、ロールフィルム状等、種々のものが挙げられる。
【００４８】
ガラス又はプラスチック基板上には記録時のトラッキングを容易にするために案内溝を形成させてもよい。また、ガラス又はプラスチック基板にはプラスチックバインダー又は無機酸化物、無機硫化物等の下引き層を設けてもよく、下引層は基板より熱伝導率の低いものが好ましい。
【００４９】
本発明の光記録媒体における記録層は、例えば、一般式（１）のジイモニウ化合物及び／又はアミニウム体、及びより好ましくは、一般式（１）のジイモニウ化合物及び／又はアミニウム体と他の有機色素を、公知の有機溶剤、例えば、テトラフルオロプロパノール（ＴＦＰ）、オクタフルオロペンタノール（ＯＦＰ）、ダイアセトンアルコール、メタノール、エタノール、ブタノール、メチルセロソルブ、エチルセロソルブ、ジクロロエタン、イソホロン、又はシクロヘキサノン等に溶解し、必要に応じて、適当なバインダーを加え、その溶液をスピンコーター、バーコーター、又はロールコーター等により基板上に塗布することにより得ることが出来る。本発明の光記録媒体における記録層は、その他の方法、例えば、真空蒸着法や、スパッタリング法、ドクターブレード法、キャスト法、又は、基板を溶液中に漬けるディッピング法によっても得ることができる。ここにおいて、バインダーとしては、アクリル系樹脂、ウレタン系樹脂、又はエポキシ系樹脂等が使用されうる。
【００５０】
記録層の膜厚は、記録感度や反射率を考慮すると、好ましくは０.０１μｍ〜５μｍ、より好ましくは０.０２μｍ〜３μｍである。
【００５１】
本発明の光記録媒体には、必要により記録層の下に下引層を、また記録層の上に保護層を設けることが出来、更に、記録層と保護層の間に反射層を設けることが出来る。反射層を設ける場合、反射層は、金、銀、銅、アルミニウム等の金属、好ましくは金、銀又はアルミニウムで構成されるが、これらの金属は単独で使用してもよく、又は２種以上の合金として使用してもよい。反射層は、真空蒸着法、スパッタリング法、イオンプレーティング法等で成膜される。このような反射層の厚さは、０.０２〜２μｍである。反射層の上に設けられることのある保護層は、一般に、紫外線硬化樹脂をスピンコート法により塗装した後、紫外線を照射し、塗膜を硬化させて形成されるものである。その他、エポキシ樹脂、アクリル樹脂、シリコーン樹脂、又はウレタン樹脂等も保護膜の形成材料に用いられる。このような保護膜の厚さは、通常、０.０１〜１００μｍである。
【００５２】
本発明の光記録媒体における情報の記録又は画像の形成は、レーザー、例えば、半導体レーザー、ヘリウム−ネオンレーザー、Ｈｅ−Ｃｄレーザー、ＹＡＧレーザー、又はＡｒレーザー等の集光したスポット状の高エネルギービームを、基板を通して又は基板と反対側から記録層に照射することにより行われ、情報又は画像の読み出しは、低出力のレーザービームを照射することにより、ピット部とピットが形成されていない部分の反射光量又は透過光量の差を検出することにより行われる。
【００５３】
本発明の近赤外線吸収フィルターは、ディスプレーの前面板の様な用途に限らず、赤外線をカットする必要があるフィルターやフィルム、例えば、断熱フィルム、光学製品、サングラス等にも使用することが出来る。
【００５４】
本発明の近赤外線吸収フィルターは、可視光領域では非常に高い透過率を示しながら、近赤外線領域は広範な波長の近赤外線を吸収する優れた近赤外線吸収フィルターである。従来の直鎖状の末端基を有するジイモニウム塩からなる近赤外線吸収フィルターに比べ、溶解度も高く、加工性も優れている。特に、本発明の近赤外線吸収化合物は耐熱性においては非常に優れており、耐熱試験中における分解などの反応を起こしにくいため、可視部の着色がほとんど起こらない近赤外線吸収フィルターを得ることができる。更に、この様な特徴を有していることから、近赤外線吸収フィルターや例えば断熱フィルム及びサングラスのような近赤外線吸収フィルムに好適に用いることができ、特に、プラズマディスプレー用の近赤外線吸収フィルターに好適である。
本発明の光記録媒体は、繰り返し再生における耐久性、耐湿熱性及び耐光安定性を著しく向上させた光記録媒体を提供することができる。
【００５５】
【実施例】
以下、本発明を実施例により更に具体的に説明するが、本発明は、これらの実施例に限定されるものではない。尚、実施例中、「部」は特に特定しない限り「重量部」を表す。
【００５６】
【合成例１】
（１） Ｎ , Ｎ , Ｎ’ , Ｎ’−テトラキス｛ｐ−ジ（ｉｓｏ−ブチル）アミノフェニル｝−ｐ−フェニレンジアミンの合成
ＤＭＦ３０部中に、Ｎ,Ｎ,Ｎ’,Ｎ’−テトラキス（アミノフェニル）−ｐ−フェニレンジアミン３.８部、ｉｓｏ−ブチルブロミド２１部、及び炭酸カリウム１５部を加え、８０℃で１時間、９０℃で７時間、及び１３０℃で１時間反応させた。冷却後、濾過し、この反応液（濾液）にイソプロパノール３０部を加え、５℃以下で１時間撹拌した。生成した結晶をメタノールで洗浄した後、乾燥し、薄茶色の結晶２.５部を得た。
融点 １５９〜１６７℃（ＤＳＣ）
【００５７】
（２） Ｎｏ . １化合物の合成
ＤＭＦ１０部中に上記（１）で合成した化合物１部を加え、６０℃に加熱溶解した後、ＤＭＦ１０部中に溶解した六フッ化アンチモン酸銀０.７８部を加え、３０分反応させた。冷却後、析出した銀を濾別した。この反応液（濾液）に水１０部をゆっくりと滴下し、滴下後１５分撹拌した。生成した黒色結晶を濾過し、５０部の水で洗浄し、得られたケーキを乾燥し、Ｎｏ.１の化合物０.５部を得た。
λｍａｘ １１０４ｎｍ（ジクロロメタン）
吸光係数 １００,０００
分解温度 ２５９℃（ＴＧ−ＤＴＡ）
【００５８】
【合成例２】
前記合成例１の（２）の反応で六フッ化アンチモン酸銀の代わりに六フッ化リン酸銀０.５８部に代えた以外は合成例１と同様に合成し、Ｎｏ.２の化合物０.５部を得た。
λｍａｘ １１０４ｎｍ（ジクロロメタン）
吸光係数 ９３,２００
分解温度 ２０５℃（ＴＧ−ＤＴＡ）
【００５９】
【合成例３】
前記合成例１の（１）の反応で、ｉｓｏ−ブチルブロミドの代わりにｉｓｏ−アミルブロミドに代えた以外は合成例１と同様に合成し、Ｎ,Ｎ,Ｎ’,Ｎ’−テトラキス｛ｐ−ジ（ｉｓｏ−アミル）アミノフェニル｝−ｐ−フェニレンジアミンを得た。
融点 １０４〜１０７℃（ＤＳＣ）
【００６０】
また、この化合物を前記合成例１の（２）の反応と同様に六フッ化アンチモン酸銀で反応させ、Ｎｏ.５化合物を得た。
λｍａｘ １１０６ｎｍ（ジクロロメタン）
吸光係数 １０９,０００
分解温度 ２７８℃（ＴＧ−ＤＴＡ）
【００６１】
【合成例４】
前記合成例３の反応で六フッ化アンチモン酸銀の代わりに六フッ化リン酸銀に代えた以外は合成例３と同様に合成し、Ｎｏ.６の化合物を得た。
λｍａｘ １１０２ｎｍ（ジクロロメタン）
吸光係数 １０７,０００
分解温度 ２２０℃（ＴＧ−ＤＴＡ）
【００６２】
その他の化合物例についても、上記合成例１と同様に対応するフェニレンジアミン誘導体を合成し、それを対応する銀塩はじめ前記した種々の酸化剤で酸化した後、対応するアニオンと反応させることにより、合成できる。
【００６３】
【実施例１】
（近赤外線吸収フィルター及び耐熱安定性試験）
テトラフルオロプロパノール１０部に前記実施例で得られたＮｏ.１、Ｎｏ.２、Ｎｏ.５及びＮｏ.６の各化合物０.１部を溶解し、その溶液約１ｍｇを、ポリカーボネート基盤に回転速度２０００ｒｐｍでスピンコートし、本発明の近赤外線吸収フィルターを得た。得られた近赤外線吸収フィルターについて、８０℃の熱風乾燥機を用いて、１日、４日、７日、１１日、及び１４日の各期間で耐熱安定性試験を行った。試験後、各近赤外線吸収フィルターに関し、色素残存率を分光光度計にて測定した。耐熱試験の結果を表４に示す。
【００６４】
尚、上記化合物の代わりにテトラキス｛ｐ−ジ（ｎ−ブチル）アミノフェニル｝フェニレンジイモニウムの六フッ化アンチモン酸塩（比較試料）を用いた以外は同様にして色素膜を作製し、評価した。
【００６５】
【表４】
【実施例２】
（近赤外線吸収フィルター）
前記実施例１で得られたＮｏ.１の化合物を、ＰＭＭＡ（ポリメタクリル酸メチル）に対して０.０３％の量で添加し、温度２００℃で射出成形し、厚さ１ｍｍと３ｍｍのフィルターを得た。得られたフィルターの８００〜１０００ｎｍでの平均光線透過率を、分光光度計にて測定したところ、厚さ１ｍｍのフィルターでは２０％、３ｍｍのフィルターでは３％であった。
【００６７】
【実施例３】
（光記録媒体及び耐熱安定性試験）
前記合成例１で得られたＮｏ.１の化合物０.０２部とシアニン色素（ＯＭ−５７、富士写真フィルム社製）０.１０部をテトラフルオロプロパノール１０部に溶解し、０.２μｍのフィルターを通過させて塗布液を得た。この溶液５ｍｌをグルーブ付５インチポリカーボネート樹脂基板上にピペットにて滴下し、スピンコーターにて塗布、乾燥し、有機薄膜記録層を形成した。塗布膜の最大吸収波長は７１９ｎｍであった。得られた塗布膜に金をスッパッタリング法で製膜して反射層を形成し、光記録媒体を作製した。得られた光記録媒体をＣＤ−Ｒ用記録再生機で評価したところ、記録及び再生が可能であった。
【００６８】
【実施例４】
テトラフルオロプロパノール１５部にシアニン色素（ＯＭ−５７）０.３部を溶解し、その溶液に、それぞれ前記各実施例で得られた、Ｎｏ.１の化合物（試料１）、Ｎｏ.２の化合物（試料２）、Ｎｏ.５の化合物（試料３）、Ｎｏ.１の化合物のアミニウム体（試料４）、及びＮｏ.２の化合物のアミニウム体（試料５）を０.０４部の量で添加し、塗液を作製した。得られた塗液をポリカーボネート基板にスピンコートし、色素膜を作製した。得られた色素膜について、先ず、６０℃・９５％ＲＨの条件下で４日間耐湿熱試験を行った。その試験が終了した後、前記色素膜をスガ試験機製紫外線ロングライフカーボンアーク耐光試験機（ブラックパネル温度６３℃）に入れ、基板側から光を照射し、１０時間、２０時間、及び４０時間の照射時間で耐光安定性試験を行った。その後、シアニン色素の残存率を分光光度計にて測定した。結果を表７に示す。
【００６９】
尚、比較の為に、Ｎｏ.１、Ｎｏ.２、及びＮｏ.５の化合物の代わりにテトラキス｛ｐ−ジ（ｎ−ブチル）アミノフェニル｝フェニレンジイモニウムの六フッ化アンチモン酸塩（比較試料１）を用い、Ｎｏ.１及びＮｏ.２の化合物のアミニウム体の代わりにテトラキス｛ｐ−ジ（ｎ−ブチル）アミノフェニル｝フェニレンアミニウムの六フッ化アンチモン酸塩（比較試料２）を用いた以外は同様にして色素膜を作製し、評価した。結果を表５に示す。また、耐湿試験を経ずに耐光試験を行った結果を表６に示す。
【００７０】
【表５】
【表６】
【発明の効果】
本発明のジイモニウム塩化合物は、従来の直鎖状の末端基を有するジイモニウム塩に比べ、溶解度が高く加工性も優れており、また、非常に耐湿熱性に優れている。これを用いた近赤外線吸収フィルターは耐熱性に極めて優れた近赤外線吸収フィルターであり、耐熱試験を行っても、該試験中に分解などの反応を起こしにくく、可視部の着色がほとんど認められない。この様な特徴を有していることから、本発明のジイモニウム塩化合物は、近赤外線吸収フィルターや、例えば断熱フィルム及びサングラスのような近赤外吸収フィルムに好適に用いることができ、特に、プラズマディスプレー用の近赤外線吸収フィルターに好適である。また、上記化合物を、例えば光記録媒体の記録層に当たる有機色素薄膜に含有させた場合、繰り返し再生における耐久性、耐湿熱性及び耐光安定性を著しく向上させた光記録媒体を提供することができる。[0001]
【Technical field】
The present invention relates to a diimonium salt compound excellent in heat resistance and having a near-infrared absorption ability, a near-infrared absorption filter, a near-infrared absorption composition, and an optical information recording medium, and in particular, a plasma comprising the near-infrared absorption filter The present invention relates to a near infrared absorption filter for a display panel.
[0002]
[Background]
Conventionally, the diimonium salt compound which is a near-infrared absorber is widely used for a near-infrared absorption filter, a heat insulation film, sunglasses, etc. However, in the conventional diimonium salt compound, there are many compounds having a linear alkyl group at the end group, and the near-infrared absorption filter using these compounds generally has a material that is easily changed by heat and light. For this reason, there was a problem that the near-infrared absorptivity decreased. Especially for heat, there was a serious problem that the visible transmittance of the filter itself decreased with decomposition and the color of the filter became greenish. Near-infrared absorption filters are also used for plasma display panels. A plasma display panel is a panel that displays an image using plasma emission, and the plasma emission includes light in the infrared region (800 to 1100 nm), and thus various infrared rays that can exist around the panel. In order to eliminate malfunctions of devices that use the remote control, such as remote controllers, automatic doors, and entry detectors, it is necessary to cut light in the infrared region using a near infrared absorption filter. However, the conventional near-infrared absorber has a problem that a satisfactory filter cannot be provided for the reasons described above.
[0003]
Also, various organic dyes such as cyanine dyes have been proposed as dyes for use in optical recording media containing organic dyes, particularly optical disks such as CD-R and DVD-R that can be recorded only once and optical cards. However, in general, there has been a problem that the recording / reproducing characteristics and the storage stability are lowered due to the fact that these dyes are easily changed by light. As means for solving such problems, it is already known to add a diimonium salt having a linear end group, as described in JP-B-6-26028 and JP-A-1-99885. ing. However, when a heat resistance test and a moist heat resistance test are performed on a recording medium prepared using these compounds, in general, the diimonium salt or the like deteriorates first, and the cyanine dye is extremely deteriorated in the subsequent light resistance test. There was a problem of becoming.
[0004]
[Problems to be solved by the invention]
The present invention has been made in view of such a situation, and an object of the present invention is to absorb near infrared rays with improved stability, particularly heat resistance, as compared with a conventional diimonium salt having a linear alkyl group. To provide a near-infrared absorption filter improved in heat resistance suitable for a near-infrared absorption filter for a plasma display panel, and an optical recording medium, prepared using the compound (dimonium salt), such a near-infrared absorption compound is there.
[0005]
DISCLOSURE OF THE INVENTION
As a result of diligent efforts to solve the above-described problems, the present inventors have found that a near-infrared absorbing compound having the structure of the following formula (1) has excellent stability, particularly excellent heat resistance. Completed the invention. That is, the present invention
(1) The following formula (1):
[0006]
[Chemical 2]
A near infrared absorbing filter comprising at least one compound represented by:
(2) Rings A and B other than the 1,4-position are unsubstituted or have 1 to 4 halogen atoms, lower alkyl groups, lower alkoxy groups, cyano groups and / or hydroxyl groups as substituents. The near-infrared absorption filter according to (1) above;
(3) R1~ R8The branched alkyl group in 1-methylethyl group, 1,1-dimethylethyl group, 1-methylpropyl group, 2-methylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl group, or The near-infrared absorption filter according to (1) or (2), which is a 2-ethylbutyl group;
(4) The near-infrared absorption filter according to any one of (1) to (3), which is for a plasma display panel;
(5) A near-infrared absorbing composition obtained by adding a compound represented by formula (1) to a resin;
(6) The following formula (1):
[0007]
[Chemical 3]
[0008]
[Formula 4]
A diimonium salt compound represented by:
(7) An optical information recording medium comprising the recording layer containing at least one diimonium salt compound according to (6) above;
About.
[0009]
DETAILED DESCRIPTION OF THE INVENTION
The near-infrared absorption filter of the present invention uses at least one compound having a structure represented by the general formula (1). In general formula (1), rings A and B may or may not have 1 to 4 substituents in addition to the 1,4-position. Examples of the substituent that can be bonded include a halogen atom, a hydroxyl group, a lower alkoxy group, a cyano group, and a lower alkyl group. Examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the lower alkoxy group include C such as methoxy group and ethoxy group.1~ C5As the lower alkyl group, for example, a C group such as a methyl group or an ethyl group can be used.1~ C5Of the alkyl group. Preferably, both A and B do not have a substituent, or are substituted with a halogen atom (especially a chlorine atom or a bromine atom), a methyl group or a cyano group. In addition, when B has a substituent, all four B rings are the same, and further, the position of the substituent is m-position with respect to the nitrogen atom bonded to the phenylenediamine skeleton. preferable. Furthermore, rings A and B preferably have no substituent other than the 1,4-position in terms of synthesis.
[0010]
In the general formula (1), R1~ R8Each may be the same or different, at least one of which is a branched alkyl group, and the remainder represents a linear alkyl group having 1 to 8 carbon atoms which may have a substituent. .
[0011]
Specific examples of such a branched alkyl group include 1-methylethyl group (i-propyl group), 1,1-dimethylethyl group (t-butyl group), 1-methylpropyl group (sec-butyl). 1,1-dimethylpropyl group, 2-methylpropyl group (iso-butyl group), 1,2-dimethylpropyl group, 2,2-dimethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, 3-methylbutyl Carbon number such as a group (iso-amyl group), 1,1-dimethylbutyl group, 2,2-dimethylbutyl group, 3,3-dimethylbutyl group, 1,2-dimethylbutyl group, and 2-ethylbutyl group Examples thereof include an alkyl group having 1 to 20 carbon atoms, preferably an alkyl group having 1 to 10 carbon atoms.
[0012]
R1~ R8The remaining substituent other than the branched alkyl group is preferably selected from linear alkyl groups having 1 to 8 carbon atoms which may have a substituent. Specific examples of these linear alkyl groups include an ethyl group, an n-propyl group, and an n-butyl group, and examples of the substituent that can be bonded to these groups include a cyano group; a hydroxyl group; Halogen atoms such as fluorine atom, chlorine atom and bromine atom; alkoxy groups having 1 to 6 carbon atoms such as methoxy group, ethoxy group, n-propoxy group and n-butoxy group; methoxymethoxy group, ethoxymethoxy group and methoxyethoxy group C2-C8 alkoxyalkoxy groups such as ethoxyethoxy group, methoxypropoxy group, methoxybutoxy group, ethoxybutoxy group; carbon such as methoxymethoxymethoxy group, methoxymethoxyethoxy group, methoxyethoxyethoxy group, ethoxyethoxyethoxy group An alkoxyalkoxy group of 3 to 15; an allyloxy group; Aryloxy groups having 6 to 12 carbon atoms such as xy group, tolyloxy group, xylyloxy group, naphthyloxy group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, etc. An alkoxycarbonyl group having 2 to 7 carbon atoms; an alkylcarbonyloxy group having 2 to 7 carbon atoms such as a methylcarbonyloxy group, an ethylcarbonyloxy group, an n-propylcarbonyloxy group, and an n-butylcarbonyloxy group; and methoxycarbonyl Examples thereof include an alkoxycarbonyloxy group having 2 to 7 carbon atoms such as an oxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, and an n-butoxycarbonyloxy group.
[0013]
R mentioned above1~ R8Among these branched alkyl substituents, preferred are, for example, 1-methylethyl group, 1,1-dimethylethyl group, 1-methylpropyl group, 2-methylpropyl group, 1-methylbutyl group, 2-methylbutyl. Group, 3-methylbutyl group, 2-ethylbutyl group and the like.
[0014]
X is an anion necessary for neutralizing the electric charge, and one molecule is required when the anion is divalent, and two molecules are required when the anion is monovalent. These anions are selected from, for example, organic acid anions or inorganic anions. Specifically, examples of the organic acid anion include organic carboxylate ions such as acetate ion, lactate ion, trifluoroacetate ion, propionate ion, benzoate ion, oxalate ion, succinate ion and stearate ion; Methanesulfonate ion, toluenesulfonate ion, naphthalene monosulfonate ion, naphthalene disulfonate ion, chlorobenzenesulfonate ion, nitrobenzenesulfonate ion, dodecylbenzenesulfonate ion, benzenesulfonate ion, ethanesulfonate ion, trifluoromethanesulfone Organic sulfonate ions such as acid ions; and organic borate ions such as tetraphenylborate ions and butyltriphenylborate ions. Preferred are trifluoromethanesulfonate ions. , Alkyl sulfonate ion, and alkyl aryl sulfonate ion such as toluenesulfonate ion.
[0015]
Examples of inorganic anions include halogen ions such as fluorine ion, chlorine ion, bromine ion and iodine ion; thiocyanate ion, hexafluoroantimonate ion, perchlorate ion, periodate ion, nitrate ion and tetrafluoroborate. Ion, hexafluorophosphate ion, molybdate ion, tungstate ion, titanate ion, vanadate ion, phosphate ion, borate ion and the like, and preferable ones include perchlorate ion, iodine ion, Tetrafluoroborate ion, hexafluorophosphate ion, hexafluoroantimonate ion and the like can be mentioned.
[0016]
Preferred examples of these anions include perchlorate ion, iodine ion, tetrafluoroborate ion, hexafluorophosphate ion, hexafluoroantimonate ion, trifluoromethanesulfonate ion, and toluenesulfonate ion. Is mentioned.
[0017]
In Formula (2), n is an integer of 1-17, Preferably it is 1-7. R is a branched alkyl group, and the number of carbon atoms as a whole of the formula (2) is 4 to 20.
[0018]
Next, specific examples of the near-infrared absorbing compound represented by the general formula (1) of the present invention are shown in Tables 1 to 3. In Tables 1 to 3, i- represents iso-, s- represents sec-, t- represents a branched state such as tert-, and TsO represents a toluenesulfonate ion. In addition, regarding A and B, when there is no substitution except for the 1,4-position, it is expressed as “4H”. R1~ R8R1~ R8Are all iso-butyl groups, ie (R1, R2), (R3, R4), (R5, R6) And (R7, R8) In which all four combinations of substituents are iso-butyl groups, “4 (i-C4H9, I-C4H9) ", And similarly all iso-amyl groups (-C2H4CH (CH3)2) Is "4 (i-C5H11, I-C5H11) ". R1~ R8Of these, for example, when one is an n-butyl group and the rest is an iso-butyl group, that is, n-butyl is included in one of four combinations of substituents, and the remaining three sets are all iso- When it is a butyl group, “3 (i-C4H9, I-C4H9) (I-C4H9, N-C4H9) ".
[0019]
In Compounds Nos. 23 and 24, all four B rings are the same, and the position of the substituent is the m-position with respect to the nitrogen atom bonded to the phenylenediamine skeleton.
[0020]
[Table 1]
[Table 2]
[Table 3]
The compound represented by the general formula (1) used in the near-infrared absorption filter of the present invention can be obtained by the following method described in, for example, Japanese Patent Publication No. 43-25335. That is, the following formula (3) obtained by reducing a product obtained by Ullmann reaction of p-phenylenediamine and 1-chloro-4-nitrobenzene:
[0024]
[Chemical formula 5]
In an organic solvent, preferably in a water-soluble polar solvent such as DMF, DMI or NMP, at 30 to 160 ° C., preferably 50 to 140 ° C., and the desired R1~ R8Halogenated compounds corresponding to (for example, R1I-C4H9In the case of BrCH2CH (CH3)2) To form all substituents (R1~ R8) Are the same (hereinafter referred to as all substituents). In addition, when synthesizing a compound other than all substituted compounds, for example, when synthesizing the compound of No. 25, a reagent having a predetermined number of moles (7 mol per mol of the amine compound of the above formula (3)) is first prepared. BrCH2CH (CH3)2) To react with R1~ R8Corresponding to the number of moles required to introduce the remaining substituent (n-butyl group) after introducing an iso-butyl group into seven of them (1 mole per mole of amine compound of the above formula (3)) Reagent (BrC4H9). Arbitrary compounds other than all substitution products can be obtained by the same method as the production method of the exemplified compound No. 25.
[0025]
Thereafter, the compound synthesized above corresponds to X in formula (1) at 0-100 ° C., preferably 5-70 ° C. in an organic solvent, preferably in a water-soluble polar solvent such as DMF, DMI or NMP. An oxidizing agent (for example, silver salt) is added to carry out the oxidation reaction. If the equivalent of the oxidizing agent is 2 equivalents, the diimonium salt compound represented by the general formula (1) of the present invention is obtained. If it is 1 equivalent, a monovalent aminium salt compound (hereinafter referred to as an aminium body) is obtained. It is done.
[0026]
Further, by oxidizing the compound synthesized above with an oxidizing agent such as silver nitrate, silver perchlorate, cupric chloride, etc., and then adding the acid or salt of the desired anion to the reaction solution, and performing salt exchange In addition, a compound represented by the general formula (1) can be synthesized.
[0027]
The near-infrared absorbing filter of the present invention may be one in which a layer containing the above-mentioned near-infrared absorbing compound is provided on a substrate, and the substrate itself contains a near-infrared absorbing compound (or a cured product thereof). ). The substrate is not particularly limited as long as it can be generally used for a near-infrared absorption filter, but a resin substrate is usually used. The thickness of the near-infrared absorbing compound-containing layer is generally about 0.1 μm to 10 mm, but is appropriately determined according to the purpose such as the near-infrared cut rate. Moreover, content of a near-infrared absorption compound is also suitably determined according to the target near-infrared cut rate.
[0028]
The resin used as the base material is preferably as highly transparent as possible when molded into a resin plate or resin film. Specific examples include polyethylene, polystyrene, polyacrylic acid, polyacrylic acid ester, polyvinyl acetate, and polyacrylonitrile. , Vinyl compounds such as polyvinyl chloride and polyvinyl fluoride, and addition polymers of these vinyl compounds; polymethacrylic acid, polymethacrylic acid ester, polyvinylidene chloride, polyvinylidene fluoride, polycylidene vinylidene, vinylidene fluoride / trifluoro Copolymers of vinyl compounds or fluorine compounds such as ethylene copolymers, vinylidene fluoride / tetrafluoroethylene copolymers, vinylidene cyanide / vinyl acetate copolymers; polytrifluoroethylene, polytetrafluoroethylene, polyhexa Fluorine-containing resins such as fluoropropylene; polyamides such as nylon 6 and nylon 66; polyimides; polyurethanes; polypeptides; polyesters such as polyethylene terephthalate; polycarbonates; polyethers such as polyoxymethylene; Examples include butyral.
[0029]
The method for producing the near-infrared absorption filter of the present invention is not particularly limited, but for example, the following method can be used. For example, (1) a method in which the above-mentioned near-infrared absorbing compound is kneaded into a resin and thermoformed to produce a resin plate or film; (2) a prepolymer of the compound and a resin monomer or a resin monomer is present in the presence of a polymerization catalyst A method of producing a resin plate or film by cast polymerization below; (3) a method of producing a paint containing the above compound and coating it on a transparent resin plate, a transparent film, or a transparent glass plate; and (4) the above For example, a compound resin is contained in an adhesive to produce a laminated resin plate, a laminated resin film, or a laminated glass plate.
[0030]
As a production method of (1), the processing temperature, filming (resin plate) conditions and the like are slightly different depending on the resin used, but the compound of the present invention is usually added to the base resin powder or pellets, and 150- Examples include a method of heating and dissolving at 350 ° C. and then molding to produce a resin plate, or forming a film (resin plate) with an extruder. The amount of the above-mentioned near infrared absorbing compound added varies depending on the thickness, absorption strength, visible light transmittance, etc. of the resin plate or film to be produced, but is generally 0.01 to 30% with respect to the weight of the binder resin. %, Preferably 0.03 to 15% by weight.
[0031]
In the method (2), which is prepared by cast polymerization of the above compound and a resin monomer or a prepolymer of a resin monomer in the presence of a polymerization catalyst, the mixture is injected into a mold and allowed to react and cure. Alternatively, it is poured into a mold and solidified until it becomes a hard product in the mold and molded. Many resins can be molded by this method, and specific examples of such resins include acrylic resins, diethylene glycol bis (allyl carbonate) resins, epoxy resins, phenol-formaldehyde resins, polystyrene resins, and silicon resins. . Among them, the casting method by bulk polymerization of methyl methacrylate, which can obtain an acrylic sheet excellent in hardness, heat resistance, and chemical resistance, is preferable.
[0032]
As the polymerization catalyst, known radical thermal polymerization initiators can be used, for example, peroxides such as benzoyl peroxide, p-chlorobenzoyl peroxide, diisopropyl peroxycarbonate, and azo compounds such as azobisisobutyronitrile. Can be mentioned. The amount used is generally from 0.01 to 5% by weight, based on the total amount of the mixture. The heating temperature in thermal polymerization is generally 40 to 200 ° C., and the polymerization time is generally about 30 minutes to 8 hours. In addition to thermal polymerization, a method of photopolymerization by adding a photopolymerization initiator or a sensitizer can also be used.
[0033]
Examples of the method (3) include a method in which the compound used in the present invention is dissolved in a binder resin and an organic solvent to form a paint, and a method in which the compound of the present invention is microparticulated and dispersed in water to obtain a water-based paint. There is. In the former method, for example, aliphatic ester resin, acrylic resin, melamine resin, urethane resin, aromatic ester resin, polycarbonate resin, polyvinyl resin, aliphatic polyolefin resin, aromatic polyolefin resin, polyvinyl alcohol resin, polyvinyl modification Resins or the like or copolymer resins thereof can be used as a binder.
[0034]
As the solvent, a halogen-based, alcohol-based, ketone-based, ester-based, aliphatic hydrocarbon-based, aromatic hydrocarbon-based, ether-based solvent, or a mixture thereof can be used. Although the density | concentration of the near-infrared absorption compound of this invention changes with thickness of the coating to produce, absorption intensity, and visible light transmittance | permeability, it is 0.1-30 weight% generally with respect to binder resin.
[0035]
Using the coating material thus produced, a near-infrared absorbing filter is obtained by coating on a transparent resin film, transparent resin plate, or transparent glass with a spin coater, bar coater, roll coater, spray, or the like. Can do.
[0036]
In the method (4), as an adhesive, a general silicon-based, urethane-based, acrylic-based resin or laminated glass polyvinyl butyral adhesive, ethylene-vinyl acetate adhesive, and other laminated glass A known transparent adhesive can be used. Transparent resin plates, resin plates and resin films, resin plates and glass, resin films, resin films and glass, or glasses using an adhesive containing 0.1 to 30% by weight of the compound of the present invention. Adhere to make a filter.
[0037]
In addition, at the time of kneading and mixing by each method, usual additives used for resin molding such as an ultraviolet absorber and a plasticizer may be added.
[0038]
Thus, in each method of (1) to (4), the near-infrared absorption composition which added this invention compound represented by Formula (1) in resin is also contained in this invention.
[0039]
The near-infrared absorption filter of the present invention preferably uses a diimonium salt compound represented by the general formula (1), but an aminium body having a corresponding structure may be used. When the aminium body is used, the aminium body may be used alone or in combination with the diimonium compound of the general formula (1). Furthermore, you may mix and produce with another near-infrared absorption compound. Examples of other near-infrared absorbing compounds that can be used in combination include phthalocyanine dyes, cyanine dyes, and dithiol nickel complexes. In addition, near-infrared absorbing compounds of inorganic metals can be used in combination. Examples of such inorganic metals include copper compounds such as copper metal, copper sulfide or copper oxide, metal mixtures based on zinc oxide, tungsten compounds, ITO, ATO, etc. are mentioned.
[0040]
In order to change the color tone of the filter, it is also preferable to add a dye having absorption in the visible region within a range that does not impair the effects of the present invention. It is also possible to produce a filter containing only the color-adjusting dye, and then attach the near-infrared absorption filter of the present invention later.
[0041]
When such a near-infrared absorption filter is used for the front plate of a display, the higher the visible light transmittance, the better, and a transmittance of at least 40% or more, preferably 50% or more is required. The near infrared cut region is preferably 800 to 900 nm, more preferably 800 to 1000 nm, and the average near infrared transmittance of the region is 50% or less, more preferably 30% or less, still more preferably 20% or less, Particularly preferably, it is desirable to be 10% or less. Therefore, it is preferable to use a diimonium compound of the general formula (1) without using an aminium body which generally has a low visible light transmittance.
[0042]
The optical recording medium of the present invention has a recording layer on a substrate, and the recording layer contains at least one diimonium compound of the general formula (1) and / or an aminium body. The diimonium compound and / or aminium compound of the general formula (1) may be used alone, but if necessary, one or more compounds selected from the compound of the general formula (1) and / or the aminium compound may be mixed. May be used.
[0043]
In the recording layer of the optical recording medium of the present invention, the diimonium compound of the general formula (1) and / or the aminium body may be contained singly or mixed with various additives such as a binder. Also good. In this case, information is recorded by the diimonium compound of the general formula (1) and / or the aminium body.
[0044]
Furthermore, the light resistance of the optical recording medium can be improved by including the diimonium compound of the general formula (1) and / or the aminium in the recording layer of the optical recording medium on which information is recorded by the organic dye. . Such an optical recording medium is also a kind of the optical recording medium of the present invention.
[0045]
In an optical recording medium using the diimonium compound and / or aminium compound of the general formula (1) for improving light resistance, organic dyes that can be used in combination with these compounds are generally known dyes, for example, Examples include cyanine dyes, squarylium dyes, indoaniline dyes, phthalocyanine dyes, azo dyes, merocyanine dyes, polymethine dyes, naphthoquinone dyes, and pyrylium dyes.
[0046]
The diimonium compound and / or aminium compound of the general formula (1) is generally used in an amount of 0.01 to 10 mol, preferably 0.03 to 3 mol, with respect to 1 mol of these organic dyes.
[0047]
The optical recording medium of the present invention has a recording layer containing a diimonium compound of the general formula (1) and / or an aminium body and, if desired, a dye, provided on a substrate. A reflective layer and a protective layer are provided as necessary. It is done. Any known substrate can be used. For example, a glass plate, a metal plate, a plastic plate or a film can be mentioned, and plastics for producing these include acrylic resins, polycarbonate resins, methacrylic resins, polysulfone resins, polyimide resins, amorphous polyolefin resins, polyester resins. And polypropylene resin. As for the shape of the substrate, various shapes such as a disk shape, a card shape, a sheet shape, and a roll film shape are exemplified.
[0048]
A guide groove may be formed on a glass or plastic substrate to facilitate tracking during recording. The glass or plastic substrate may be provided with a subbing layer such as a plastic binder, inorganic oxide, or inorganic sulfide, and the subbing layer preferably has a lower thermal conductivity than the substrate.
[0049]
The recording layer in the optical recording medium of the present invention is, for example, a dimonium compound and / or aminium compound of the general formula (1), and more preferably a dimonium compound and / or aminium compound of the general formula (1) and other organic dyes. Is dissolved in a known organic solvent such as tetrafluoropropanol (TFP), octafluoropentanol (OFP), diacetone alcohol, methanol, ethanol, butanol, methyl cellosolve, ethyl cellosolve, dichloroethane, isophorone, or cyclohexanone. If necessary, an appropriate binder can be added, and the solution can be obtained by applying the solution onto a substrate with a spin coater, bar coater, roll coater or the like. The recording layer in the optical recording medium of the present invention can also be obtained by other methods, for example, vacuum deposition, sputtering, doctor blade, casting, or dipping in which the substrate is immersed in a solution. Here, an acrylic resin, a urethane resin, an epoxy resin, or the like can be used as the binder.
[0050]
The film thickness of the recording layer is preferably 0.01 μm to 5 μm, more preferably 0.02 μm to 3 μm in consideration of recording sensitivity and reflectance.
[0051]
In the optical recording medium of the present invention, if necessary, an undercoat layer can be provided below the recording layer, and a protective layer can be provided on the recording layer, and a reflective layer can be provided between the recording layer and the protective layer. I can do it. When the reflective layer is provided, the reflective layer is made of a metal such as gold, silver, copper, or aluminum, preferably gold, silver, or aluminum, but these metals may be used alone or in combination It may be used as an alloy. The reflective layer is formed by a vacuum deposition method, a sputtering method, an ion plating method, or the like. The thickness of such a reflective layer is 0.02 to 2 μm. The protective layer that may be provided on the reflective layer is generally formed by applying an ultraviolet curable resin by a spin coating method and then irradiating the ultraviolet ray to cure the coating film. In addition, an epoxy resin, an acrylic resin, a silicone resin, a urethane resin, or the like is also used as a protective film forming material. The thickness of such a protective film is usually 0.01-100 μm.
[0052]
The recording of information or the formation of images on the optical recording medium of the present invention is carried out by using a focused spot-like high-energy beam such as a laser, for example, a semiconductor laser, a helium-neon laser, a He-Cd laser, a YAG laser, or an Ar laser. Is irradiated to the recording layer through the substrate or from the opposite side of the substrate, and the reading of information or image is performed by irradiating a low-power laser beam to reflect the pit portion and the portion where no pit is formed. This is done by detecting the difference in light quantity or transmitted light quantity.
[0053]
The near-infrared absorption filter of the present invention can be used not only for applications such as the front plate of a display but also for filters and films that need to cut infrared rays, such as heat insulating films, optical products, and sunglasses.
[0054]
The near-infrared absorption filter of the present invention is an excellent near-infrared absorption filter that absorbs a wide range of wavelengths of near-infrared light while exhibiting very high transmittance in the visible light region. Compared with a near-infrared absorption filter made of a diimonium salt having a linear end group, the solubility is high and the processability is also excellent. In particular, the near-infrared absorbing compound of the present invention is very excellent in heat resistance and hardly undergoes a reaction such as decomposition during a heat resistance test, so that a near-infrared absorbing filter that hardly causes coloring in the visible region can be obtained. . Furthermore, since it has such characteristics, it can be suitably used for a near infrared absorption filter and a near infrared absorption film such as a heat insulating film and sunglasses, particularly for a near infrared absorption filter for plasma display. Is preferred.
The optical recording medium of the present invention can provide an optical recording medium having remarkably improved durability, resistance to moist heat and light resistance during repeated reproduction.
[0055]
【Example】
EXAMPLES Hereinafter, the present invention will be described more specifically with reference to examples, but the present invention is not limited to these examples. In the examples, “parts” represents “parts by weight” unless otherwise specified.
[0056]
[Synthesis Example 1]
(1) N , N , N ' , Synthesis of N′-tetrakis {p-di (iso-butyl) aminophenyl} -p-phenylenediamine
In 30 parts of DMF, 3.8 parts of N, N, N ′, N′-tetrakis (aminophenyl) -p-phenylenediamine, 21 parts of iso-butyl bromide, and 15 parts of potassium carbonate are added, and then at 80 ° C. for 1 hour. , Reacted at 90 ° C. for 7 hours and at 130 ° C. for 1 hour. After cooling, the mixture was filtered, 30 parts of isopropanol was added to the reaction solution (filtrate), and the mixture was stirred at 5 ° C. or lower for 1 hour. The produced crystals were washed with methanol and dried to obtain 2.5 parts of light brown crystals.
Melting point 159-167 ° C (DSC)
[0057]
(2) No . Synthesis of one compound
1 part of the compound synthesized in the above (1) was added to 10 parts of DMF, heated and dissolved at 60 ° C., 0.78 parts of silver hexafluoroantimonate dissolved in 10 parts of DMF was added and reacted for 30 minutes. After cooling, the precipitated silver was filtered off. To this reaction liquid (filtrate), 10 parts of water was slowly added dropwise, followed by stirring for 15 minutes. The produced black crystals were filtered, washed with 50 parts of water, and the resulting cake was dried to obtain 0.5 parts of No. 1 compound.
λmax 1104nm (dichloromethane)
Absorption coefficient 100,000
Decomposition temperature 259 ° C (TG-DTA)
[0058]
[Synthesis Example 2]
Compound No. 2 was synthesized in the same manner as in Synthesis Example 1 except that in the reaction of Synthesis Example 1 (2), 0.56 parts of silver hexafluorophosphate was used instead of silver hexafluoroantimonate. .5 parts were obtained.
λmax 1104nm (dichloromethane)
Absorption coefficient 93,200
Decomposition temperature 205 ° C (TG-DTA)
[0059]
[Synthesis Example 3]
Synthesis was performed in the same manner as in Synthesis Example 1 except that in the reaction of Synthesis Example 1 (1), iso-amyl bromide was used instead of iso-butyl bromide, and N, N, N ′, N′-tetrakis.Sup-Di (iso-amyl) aminophenyl}-p-Phenylenediamine was obtained.
Melting point 104-107 ° C (DSC)
[0060]
Further, this compound was reacted with silver hexafluoroantimonate in the same manner as in the reaction (2) of Synthesis Example 1 to obtain a No. 5 compound.
λmax 1106nm (dichloromethane)
Absorption coefficient 109,000
Decomposition temperature 278 ° C (TG-DTA)
[0061]
[Synthesis Example 4]
The compound of No. 6 was obtained by synthesizing in the same manner as in Synthesis Example 3 except that silver hexafluorophosphate was replaced with silver hexafluoroantimonate in the reaction of Synthesis Example 3.
λmax 1102 nm (dichloromethane)
Absorption coefficient 107,000
Decomposition temperature 220 ° C (TG-DTA)
[0062]
For other compound examples, the corresponding phenylenediamine derivative was synthesized in the same manner as in Synthesis Example 1, and after oxidizing the corresponding silver salt and other various oxidizing agents as described above, the reaction with the corresponding anion was performed. Can be synthesized.
[0063]
[Example 1]
(Near infrared absorption filter and heat stability test)
In 10 parts of tetrafluoropropanol, 0.1 part of each of the compounds No. 1, No. 2, No. 5 and No. 6 obtained in the above examples was dissolved, and about 1 mg of the solution was rotated on a polycarbonate substrate. Spin coating was performed at 2000 rpm to obtain a near infrared absorption filter of the present invention. About the obtained near-infrared absorption filter, the heat stability test was done in each period of 1st, 4th, 7th, 11th, and 14th using a 80 degreeC hot air dryer. After the test, the dye residual ratio was measured with a spectrophotometer for each near infrared absorption filter. Table 4 shows the results of the heat resistance test.
[0064]
A dye film was prepared and evaluated in the same manner except that tetrakis {p-di (n-butyl) aminophenyl} phenylenediimonium hexafluoride antimonate (comparative sample) was used instead of the above compound.
[0065]
[Table 4]
[Example 2]
(Near infrared absorption filter)
The No. 1 compound obtained in Example 1 was added in an amount of 0.03% to PMMA (polymethyl methacrylate), injection molded at a temperature of 200 ° C., and a filter having a thickness of 1 mm and 3 mm. Got. When the average light transmittance at 800 to 1000 nm of the obtained filter was measured with a spectrophotometer, it was 20% for a filter having a thickness of 1 mm and 3% for a filter having a thickness of 3 mm.
[0067]
[Example 3]
(Optical recording medium and heat stability test)
0.02 parts of the No. 1 compound obtained in Synthesis Example 1 and 0.10 parts of cyanine dye (OM-57, manufactured by Fuji Photo Film Co., Ltd.) were dissolved in 10 parts of tetrafluoropropanol, and a 0.2 μm filter was obtained. Was passed through to obtain a coating solution. 5 ml of this solution was dropped with a pipette onto a 5 inch polycarbonate resin substrate with a groove, and applied and dried with a spin coater to form an organic thin film recording layer. The maximum absorption wavelength of the coating film was 719 nm. A gold layer was formed on the obtained coating film by a sputtering method to form a reflective layer, thereby producing an optical recording medium. When the obtained optical recording medium was evaluated with a CD-R recording / reproducing apparatus, recording and reproduction were possible.
[0068]
[Example 4]
In 15 parts of tetrafluoropropanol, 0.3 part of cyanine dye (OM-57) was dissolved, and the compounds No. 1 (sample 1) and No. 2 obtained in the respective examples were respectively added to the solutions. (Sample 2), No. 5 compound (Sample 3), No. 1 compound aminium body (Sample 4), and No. 2 compound aminium body (Sample 5) were added in an amount of 0.04 parts. Then, a coating liquid was prepared. The obtained coating liquid was spin-coated on a polycarbonate substrate to prepare a dye film. The obtained dye film was first subjected to a moisture and heat resistance test for 4 days under conditions of 60 ° C. and 95% RH. After the test was completed, the dye film was placed in a UV long life carbon arc light resistance tester (black panel temperature 63 ° C.) manufactured by Suga Test Instruments, and irradiated with light from the substrate side for 10 hours, 20 hours, and 40 hours. The light stability test was performed at the irradiation time. Thereafter, the residual ratio of the cyanine dye was measured with a spectrophotometer. The results are shown in Table 7.
[0069]
For comparison, tetrakis {p-di (n-butyl) aminophenyl} phenylenediimonium hexafluoroantimonate (Comparative Sample 1) instead of the compounds No. 1, No. 2 and No. 5 ) And tetrakis {p-di (n-butyl) aminophenyl} phenyleneaminium hexafluoroantimonate (Comparative Sample 2) was used instead of the aminium bodies of the compounds No. 1 and No. 2. Except for the above, a dye film was prepared and evaluated in the same manner. The results are shown in Table 5. In addition, Table 6 shows the results of the light resistance test without passing the moisture resistance test.
[0070]
[Table 5]
[Table 6]
【The invention's effect】
The diimonium salt compound of the present invention has higher solubility and excellent processability than the conventional diimonium salt having a linear end group, and is very excellent in heat and heat resistance. Near-infrared absorption filter using this is a near-infrared absorption filter with extremely excellent heat resistance. Even when a heat test is conducted, it is difficult to cause a reaction such as decomposition during the test, and almost no coloring in the visible part is observed. . Because of having such characteristics, the diimonium salt compound of the present invention can be suitably used for a near-infrared absorbing filter, a near-infrared absorbing film such as a heat insulating film and sunglasses, in particular, plasma. Suitable for near infrared absorption filter for display. Further, when the above-mentioned compound is contained in, for example, an organic dye thin film corresponding to the recording layer of the optical recording medium, it is possible to provide an optical recording medium having remarkably improved durability in repeated reproduction, heat and humidity resistance and light stability.
Claims (4)
で示される少なくとも一種の化合物を含有することを特徴とする近赤外線吸収フィルター。Following formula (1):
The near-infrared absorption filter characterized by containing the at least 1 type of compound shown by these.
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| JP2001344714 | 2001-11-09 | ||
| PCT/JP2002/006698 WO2003005076A1 (en) | 2001-07-04 | 2002-07-02 | Diimonium salt compound, and near-infrared ray absorbing filter and optical information recording medium |
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| JPS4325335B1 (en) * | 1963-05-16 | 1968-11-01 | ||
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-
2002
- 2002-07-02 JP JP2003510997A patent/JP3699464B2/en not_active Expired - Fee Related
- 2002-07-02 EP EP02741400A patent/EP1403666A4/en not_active Withdrawn
- 2002-07-02 US US10/481,344 patent/US20040137367A1/en not_active Abandoned
- 2002-07-02 CN CNB028135873A patent/CN1257415C/en not_active Expired - Fee Related
- 2002-07-02 WO PCT/JP2002/006698 patent/WO2003005076A1/en active Application Filing
- 2002-07-04 TW TW091114807A patent/TWI319778B/en not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| TWI319778B (en) | 2010-01-21 |
| CN1529828A (en) | 2004-09-15 |
| EP1403666A8 (en) | 2004-09-08 |
| EP1403666A4 (en) | 2008-04-16 |
| CN1257415C (en) | 2006-05-24 |
| WO2003005076A1 (en) | 2003-01-16 |
| EP1403666A1 (en) | 2004-03-31 |
| JPWO2003005076A1 (en) | 2004-10-28 |
| US20040137367A1 (en) | 2004-07-15 |
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